Samm Tillotson is a commercial litigator at an elite law firm, where she spends a lot of time defending class action lawsuits for insurance clients. While she doesn't go to trial often, she spends a lot of time in court, preparing for court, and negotiating. Despite the firm's size, Samm's cases are leanly staffed, which means she works a case from beginning to end. She talks a bit about her love of discovery, work-life balance, and partnership. Samm is a graduate of the University of Denver Sturm College of Law.

This episode is hosted by Katya Valasek.

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For Katie King, investigations have always been at the center of her work. As a federal prosecutor turned Title IX and institutional equity expert, she’s spent her legal career tasked with piecing together the truth. Katie now serves as a senior administrator at Cornell University – a job that does not require a law degree or license. In this episode, Katie shares her journey into the world of civil rights law, from handling Title IX cases to overseeing compliance in areas like discrimination and employee accommodations. Katie talks about the need for constant learning and the challenges of navigating an emotional workload. Katie is a graduate of New York University School of Law.

This episode is hosted by Katya Valasek.

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Tijana Brien, a partner at the elite law firm Cooley, specializes in high-stakes securities litigation. In this episode, she unpacks the complexities of defending major corporations, discussing the importance of motions to dismiss, investigation, and focusing on the elements of a case. She shares how she navigates the challenge of translating complex technological concepts—like encryption—into accessible arguments that judges can readily comprehend, drawing from her experience representing companies such as Zoom. TIjana also reflects on how her role has evolved from detailed casework as an associate to more big-picture strategy as a partner, although she still spends more time in the weeds than more senior partners. She talks about managing the pressures of biglaw and the importance of teamwork in a high-stakes environment. Tijana is a graduate of Santa Clara University School of Law.

This episode is hosted by Kyle McEntee.

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As a “dirt lawyer,” Don Pinto’s cases typically involve one party that wants to do something in real estate, and another party trying to stop it. Whether coastal erosion or view obstruction with residential homeowners, or developers seeking to build new commercial or residential property, disputes end up in court if he can’t help his clients come to terms sooner. Each day on the job looks different, from delving into historical records for title disputes to navigating complex cases involving difficult expert witness and judges who cannot help get into the weeds on a very specialized area of law. Don also talks about how the business of real estate law has changed as land values increase, and the unexpected downsides of transparency in law firm compensation—where open financials can breed tension and rivalry among colleagues. Don is a graduate of Suffolk University Law School.

This episode is hosted by Kyle McEntee.

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Lynette Paczkowski is a litigator at heart, and her career journey has taken her to the world of probate litigation. When a will is contested, the legal battle is rarely just about money—it’s about trust, family dynamics, and sometimes the question of whether someone "pulled a fast one." In this episode, Lynette walks us through the complexities of her practice, from uncovering undue influence to determining if a codicil is legally valid. We explore how lawyers strategize, what makes a case worth fighting, and why these disputes can be so emotionally charged. As a partner on the domestic relations team at her mid-sized general practice firm, she also provides helpful insights about the business operations of her firm and its internal dynamics. Lynette is a graduate of Boston College Law School. 

This episode is hosted by Katya Valasek.

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Adam Deutsch is a personal injury lawyer who litigates medical malpractice claims...and he loves what he does. Although he opted for lawyer rather than doctor, he spends his days researching areas of medicine and consulting with experts before negotiating settlements and arguing in court. In this episode, Adam talks about medical rabbit holes, his strategy for jury selection, and the challenges that come with navigating emotional malpractice cases. Plus, he discusses how plaintiff-style compensation helps him find a true work-life balance. Adam is a graduate of Brooklyn Law School. 

This episode is hosted by Kyle McEntee.

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Former Biglaw attorney Cece Xie shares her unconventional journey from practicing law to building a portfolio career. After graduating law school, she embarked on a well-traveled road to a large law firm with a shiny name. Though she has many positive things to say about her two firms, she ultimately stepped away from it all. In this episode, Cece talks about the challenges of leaving a stable career, navigating financial uncertainty and opinionated parents, and finding purpose beyond traditional legal work. Plus, she talks about her love of writing, her book deal, and how she ultimately returned to law on her own terms. Cece is a graduate of Harvard Law School.

This episode is hosted by Katya Valasek.

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Juan Dawson is a junior associate at a newly merged megafirm. He’s one of the firm’s many energy industry lawyers – or, as he puts it, a "lawyer for electrons." In this episode, Juan shares how he pivoted to a niche, multi-faceted field involving regulatory compliance and interaction with government agencies. Juan discusses how he reconciles his initial public interest aspirations with a corporate environment. He also touches on collaboration with scientists and engineers, on-campus interviewing, and adjusting to the workload and culture of a large law firm. Despite a steep learning curve, Juan hopes the constructive criticism he receives and his effort to learn will soon help him do more client-facing work and expand his involvement in impactful projects. Juan is a graduate of Villanova University Charles Widger School of Law.  

This episode is hosted by Katya Valasek. 

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Victoria Nauman is a very recent law school graduate and state public defender. Like many law students, she entered law school intending to do some sort of public service, but lacking specificity. This episode focuses on her transition to practice. Victoria discusses some early career challenges, including imposter syndrome, building trust with clients, how she balances kindness and collegiality with being adversarial when necessary, and maintaining a work-life balance. She also candidly discusses financial realities for public defenders. Victoria is a graduate of William & Mary Law School.

This episode is hosted by Kyle McEntee.

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In this episode, Josh Offenhartz takes us through his career journey, marked by numerous transitions between law firms, sometimes sooner than he anticipated. From navigating generational differences in firm cultures to managing the evolving dynamics of career progression, client relationships, and work-life balance, Josh shares how his ability to adapt and recognize key opportunities has been integral to his progression. He candidly discusses the challenges that come with firm economics shifting unexpectedly, highlighting what happens when your goals collide with your employer's evolving challenges and priorities. Josh reflects on how stayed attuned to the surrounding opportunities and knew when it was time to move on. Concluding with his most recent transition, he reveals how his security of position at his immediately-prior firm ultimately led him to find a better fit. Josh is a graduate of Arizona State University's Sandra Day O'Connor College of Law.

This episode is hosted by Katya Valasek.

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